diff --git a/src/System.Management.Automation/engine/LanguagePrimitives.cs b/src/System.Management.Automation/engine/LanguagePrimitives.cs
index 30b7dd26660..eb44031531c 100644
--- a/src/System.Management.Automation/engine/LanguagePrimitives.cs
+++ b/src/System.Management.Automation/engine/LanguagePrimitives.cs
@@ -3581,20 +3581,20 @@ internal object Convert(object valueToConvert,
                                     TypeTable backupTable)
             {
                 IList resultAsList = null;
-                int listSize = 0;
                 Array array = null;
 
                 try
                 {
-                    // typeof(Array).IsAssignableFrom(typeof(object[])) == true
-                    if ((IsScalar) || (!(valueToConvert is Array)))
+                    int listSize = 0;
+                    if (IsScalar)
                     {
                         listSize = 1;
                     }
                     else
                     {
-                        array = (Array)valueToConvert;
-                        listSize = array.Length;
+                        // typeof(Array).IsAssignableFrom(typeof(object[])) == true
+                        array = valueToConvert as Array;
+                        listSize = array != null ? array.Length : 1;
                     }
 
                     resultAsList = ListCtorLambda(listSize);
@@ -3610,7 +3610,7 @@ internal object Convert(object valueToConvert,
                 {
                     resultAsList.Add(valueToConvert);
                 }
-                else if (listSize == 1)
+                else if (array == null)
                 {
                     object convertedValue = LanguagePrimitives.ConvertTo(valueToConvert, ElementType, formatProvider);
                     resultAsList.Add(convertedValue);
diff --git a/test/powershell/Language/Parser/Conversions.Tests.ps1 b/test/powershell/Language/Parser/Conversions.Tests.ps1
index 37efea9cfad..6aca007f90a 100644
--- a/test/powershell/Language/Parser/Conversions.Tests.ps1
+++ b/test/powershell/Language/Parser/Conversions.Tests.ps1
@@ -20,4 +20,56 @@ Describe 'conversion syntax' -Tags "CI" {
         # This test relies on the fact that there are overloads (at least 2) for ToString method.
         ([System.Management.Automation.ActionPreference]"Stop").ToString() | Should Be "Stop"
     }
+
+    Context "Cast object[] to more narrow generic collection" {
+        BeforeAll {
+            $testCases1 = @(
+                ## It's intentional to have 'Command' to be `{$result = ...}` and run it with `. $Command`.
+                ## This is because `$result = & {[List[int]]@(1,2)}` will cause the resulted List to be unraveled,
+                ## and in that case `$result` would be just an object array.
+                ## To prevent unraveling, Command needs to be `{, [List[int]]@(1,2)}`, but then the test case title
+                ## would become `, [List[int]]@(1,2)`, which is more confusing than `$result = [List[int]]@(1,2)`.
+                ## This is why the current form of `$result = [List[int]]@(1,2)` is used intentionally here.
+
+                @{ Command = {$result = [Collections.Generic.List[int]]@(1)};       CollectionType = 'List`1'; ElementType = "Int32";  Elements = @(1) }
+                @{ Command = {$result = [Collections.Generic.List[int]]@(1,2)};     CollectionType = 'List`1'; ElementType = "Int32";  Elements = @(1,2) }
+                @{ Command = {$result = [Collections.Generic.List[int]]"4"};        CollectionType = 'List`1'; ElementType = "Int32";  Elements = @(4) }
+                @{ Command = {$result = [Collections.Generic.List[int]]@("4","5")}; CollectionType = 'List`1'; ElementType = "Int32";  Elements = @(4,5) }
+
+                @{ Command = {$result = [Collections.Generic.List[string]]@(1)};    CollectionType = 'List`1'; ElementType = "String"; Elements = @("1") }
+                @{ Command = {$result = [Collections.Generic.List[string]]@(1,2)};  CollectionType = 'List`1'; ElementType = "String"; Elements = @("1","2") }
+                @{ Command = {$result = [Collections.Generic.List[string]]1};       CollectionType = 'List`1'; ElementType = "String"; Elements = @("1") }
+                @{ Command = {$result = [Collections.Generic.List[string]]@("4")};  CollectionType = 'List`1'; ElementType = "String"; Elements = @("4") }
+
+                @{ Command = {$result = [System.Collections.ObjectModel.Collection[int]]@(1)};       CollectionType = 'Collection`1'; ElementType = "Int32"; Elements = @(1) }
+                @{ Command = {$result = [System.Collections.ObjectModel.Collection[int]]@(1,2)};     CollectionType = 'Collection`1'; ElementType = "Int32"; Elements = @(1,2) }
+                @{ Command = {$result = [System.Collections.ObjectModel.Collection[int]]"4"};        CollectionType = 'Collection`1'; ElementType = "Int32"; Elements = @(4) }
+                @{ Command = {$result = [System.Collections.ObjectModel.Collection[int]]@("4","5")}; CollectionType = 'Collection`1'; ElementType = "Int32"; Elements = @(4,5) }
+
+                @{ Command = {$result = [Collections.Generic.List[System.IO.FileInfo]]@('TestFile')};
+                    CollectionType = 'List`1'; ElementType = "FileInfo";  Elements = @('TestFile') }
+                @{ Command = {$result = [Collections.Generic.List[System.IO.FileInfo]]@('TestFile1', 'TestFile2')};
+                    CollectionType = 'List`1'; ElementType = "FileInfo";  Elements = @('TestFile1', 'TestFile2') }
+                @{ Command = {$result = [Collections.Generic.List[System.IO.FileInfo]]'TestFile'};
+                    CollectionType = 'List`1'; ElementType = "FileInfo";  Elements = @('TestFile') }
+            )
+        }
+
+        It "<Command>" -TestCases $testCases1 {
+            param($Command, $CollectionType, $ElementType, $Elements)
+
+            $result = $null
+            . $Command
+
+            $result | Should Not BeNullOrEmpty
+            $result.GetType().Name | Should Be $CollectionType
+
+            $genericArgs = $result.GetType().GetGenericArguments()
+            $genericArgs.Length | Should Be 1
+            $genericArgs[0].Name | Should Be $ElementType
+
+            $result.Count | Should Be $Elements.Length
+            $result -join ";" | Should Be ($Elements -join ";")
+        }
+    }
 }